Dicyclohexylcarbodiimide → HCID 131710172, compound

HRID 1606833Notes

Reaction equation

HRID 1606833 reaction equation
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[NH2:24][C@H:25]([C:27]([NH:29][C@H:30]([C:40]([NH:42][C@H:43]([C:52]([NH:54][C@H:55]([C:65]([NH:67][C@H:68]([C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:69][O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:66])[CH2:56][CH2:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:53])[CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:41])[CH2:31][CH2:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:28])[CH3:26].FC1C(O)=C(F)C(F)=C(F)C=1F.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:24][C@H:25]([C:27]([NH:29][C@H:30]([C:40]([NH:42][C@H:43]([C:52]([NH:54][C@H:55]([C:65]([NH:67][C@H:68]([C:75]([O:77][C:78]([CH3:79])([CH3:81])[CH3:80])=[O:76])[CH2:69][O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:66])[CH2:56][CH2:57][C:58](=[O:64])[O:59][C:60]([CH3:61])([CH3:62])[CH3:63])=[O:53])[CH2:44][C:45](=[O:51])[O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:41])[CH2:31][CH2:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:28])[CH3:26])=[O:13])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 53645221HCID 53645221, compoundHCID 131710171HCID 131710171, compound

Product 1

HCID 131710172HCID 131710172, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.59 g. (8 mmoles) of Z-Asn-Gly-OH, 6.65 g. (8 mmoles) of H-Ala-Glu(OtBu)-Asp(OtBu)-Glu(OtBu)-Ser(tBu)-OtBu and 4.86 g. of pentafluorophenol are dissolved in 28 ml. of DMF. The solution is cooled to 0° C, and 1.81 g. (8.8 mmoles) of DCC are added to it. The reaction mixture is stirred at 0° C for 0.5 hours, and stirring is continued at room temperature for 2.5 hours. The separated DCU is removed by filtration; the filtrate is evaporated to dryness, and the residue is triturated with ethyl acetate. 7.3 g. (80.5 %) of Z-25-31-OtBu are obtained. M.p.: 194° C (under decomposition), Rf3 = 0.6.

Workup

  1. stirringstirring
  2. waitis continued at room temperature for 2.5 hours
  3. customThe separated DCU is removed by filtration
  4. customthe filtrate is evaporated to dryness
  5. customthe residue is triturated with ethyl acetate

Sources & evidence

ORD record
ord-87e4fc0c9b1e496a9306eae40ce05728
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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